36169-68-3

Upstream product

• 60907-91-7 2-furyl(phenyl)methanol 
• 98-01-1 furfural 
• 100-52-7 benzaldehyde 
• 113565-51-8 (R)-2-furylphenylmethanol 

Downstream Products

• 50768-10-0 pyranulose acetate 
• 303156-55-0 6-tert-butoxy-2-phenyl-2H-pyran-3-one 

Relevant academic research and scientific papers

Catalytic Environmentally Friendly Protocol for Achmatowicz Rearrangement

The increasing interest in Achmatowicz rearrangement in organic synthesis calls for a more environmentally friendly protocol since the most popular oxidants m-CPBA and NBS produced stoichiometric organic side product (m-chlorobenzoic acid or succinimide). Mechanism-guided analysis enables us to develop a new catalytic method (Oxone/KBr) for AchR in excellent yield with K2SO4 as the only side product, which greatly facilitates the purification. This protocol was integrated with other transformations, leading to a rapid access to the highly functionalized dihydropyranones.

A Biocatalytic Aza-Achmatowicz Reaction

A catalytic, enzyme-initiated (aza-) Achmatowicz reaction is presented. The involvement of a robust vanadium-dependent peroxidase from Curvularia inaequalis allows the simple use of H2O2 and catalytic amounts of bromide.

Synthesis method of polysubstituted 3-hydroxy-2-pyranone

The present invention relates to a polysubstituted 3-hydroxy-2-pyranone synthesis method, which comprises the steps below, S1 of formula (I.) compound by Achmatowicz rearrangement reaction, to give a compound of formula (II.); S2 of formula (II.) compound

Fenton chemistry for Achmatowicz rearrangement

Achmatowicz rearrangement (AchR) is a very important transformation for the synthesis of various heterocyclic building blocks and natural products. Here, the discovery of Fenton chemistry for AchR using a bifunctional catalyst (FeBr2 or CeBrsu

Divergent Synthesis of Dihydropyranone Stereoisomers via N-Heterocyclic Carbene Catalysis

We recently developed a novel chiral N-heterocyclic carbene (NHC) catalyzed dynamic kinetic enantioselective acylation (DKEA) and dynamic kinetic diastereoselective acylation (DKDA) of Achmatowicz rearrangement products to generate useful intermediates for the further synthesis of carbohydrates. In this update, we describe a divergent NHC catalytic strategy for the stereoselective preparation of all four isomers starting from a common racemic precursor. The present report provides easy access to diverse optically pure dihydropyranones. (Figure presented.).

Chloroperoxidase-Catalyzed Achmatowicz Rearrangements

Chloroperoxidase from Caldariomyces fumago catalyzes the selective oxidation of furfuryl alcohols in an Achmatowicz-type ring expansion. In combination with glucose oxidase as oxygen-activating biocatalyst, a purely enzymatic, aerobic protocol for the synthesis of 6-hydroxypyranone building blocks is obtained. Thanks to an only modest stereochemical bias of the oxygenating heme protein, optically active alcohols of either configuration are converted without a significant mismatch opening up opportunities for enantioselective multienzymatic cascades. Balancing the oxidase-driven aerobic activation, extended enzyme half-lives and productive conversion of poorly soluble and slowly reacting substrates can be achieved with high yields of the six-membered O-heterocycles.

Two catalytic protocols for Achmatowicz rearrangement using cyclic diacyl peroxides as oxidants

In situ generated bromonium-catalyzed and visible-light photocatalytic Achmatowicz rearrangements of furfuryl alcohols using cyclic diacyl peroxides as oxidants are described. Both protocols feature broad substrate scope, excellent functional group tolera

Visible-light-mediated achmatowicz rearrangement

Visible-light-mediated photoredox catalysis is a viable method to access highly reactive intermediates from cheap, readily available, and shelfstable reagents to perform clean chemical transformations. Here, we report the first photoredox-catalyzed Achmatowicz reaction of furfuryl alcohol derivatives to produce functionalized dihydropyranones while only forming easily separable NaHSO4 as a byproduct. The water solubility of the byproduct facilitates direct Boc-protection of the resulting hemiacetal without the need for column purification. The reaction is very robust and permits the use of various aqueous solutions and light sources including sunlight.

Iridium-Catalyzed Dynamic Kinetic Isomerization: Expedient Synthesis of Carbohydrates from Achmatowicz Rearrangement Products

A highly stereoselective dynamic kinetic isomerization of Achmatowicz rearrangement products was discovered. This new internal redox isomerization provided ready access to key intermediates for the enantio- and diastereoselective synthesis of a series of naturally occurring sugars. The nature of the de novo synthesis also enables the preparation of both enantiomers.

A new simple procedure for the isomerization of 2-furylcarbinols to cyclopentenones

The previously reported acid catalyzed isomerization of 2-furylcarbinols to 5-alkyl-4-hydroxycyclopent-2-enones was performed in boiling water in the absence of any acid catalyst. In this case the reaction led to the formation of more stable isomer 2-alky